37442

Sigma-Aldrich

Dihydroxyacetone phosphate lithium salt

≥95.0% (TLC)

Synonym(s):
DHAP, Glycerone phosphate lithium salt, 1-Hydroxy-3-(phosphonooxy)-2-propanone lithium salt
Empirical Formula (Hill Notation):
C3H7O6P · xLi+
CAS Number:
Molecular Weight:
170.06 (free acid basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥95.0% (TLC)

form

powder

storage temp.

−20°C

SMILES string

OCC(COP(O)(O)=O)=O

InChI

1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)

InChI key

GNGACRATGGDKBX-UHFFFAOYSA-N

Biochem/physiol Actions

Dihydroxyacetone phosphate (DHAP) is a metabolic intermediate involved in many pathways, including glycolysis, gluconeogenesis, glycerol metabolism, phosphatidic acid synthesis, fat metabolism, and the Calvin cycle.

Analysis Note

may contain up to 2-mol-equivalents water

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Glycerolipid biosynthesis in peroxisomes via the acyl dihydroxyacetone phosphate pathway.
A K Hajra et al.
Annals of the New York Academy of Sciences, 386, 170-182 (1982-01-01)
Jun Ogawa et al.
Bioscience, biotechnology, and biochemistry, 67(4), 933-936 (2003-06-06)
2-Deoxyribose 5-phosphate was produced from acetaldehyde and dihydroxyacetone phosphate via D-glyceraldehyde 3-phosphate by Klebsiella pneumoniae B-4-4 through deoxyriboaldolase- and triosephosphate isomerase-catalyzing reactions. Under the optimum conditions, 98.7 mM 2-deoxyribose 5-phosphate was produced from 200 mM acetaldehyde and 117 mM dihydroxyacetone...
John P Richard
ACS chemical biology, 3(10), 605-607 (2008-10-22)
Gluconeogenesis is blocked in a strain of Escherichia coli that is deficient in triosephosphate isomerase, but it was restored by the insertion of a plasmid coding for an L-glyceraldehyde 3-phosphate reductase (YghZ). This reductase provides a "bypass" that produces dihydroxyacetone...
John P Richard
Biochemistry, 51(13), 2652-2661 (2012-03-14)
Triosephosphate isomerase (TIM) catalyzes the stereospecific 1,2-proton shift at dihydroxyacetone phosphate (DHAP) to give (R)-glyceraldehyde 3-phosphate through a pair of isomeric enzyme-bound cis-enediolate phosphate intermediates. The chemical transformations that occur at the active site of TIM were well understood by...
Giovanni Covaleda-Cortés et al.
Marine drugs, 17(9) (2019-09-01)
A very powerful proteinaceous inhibitor of metallocarboxypeptidases has been isolated from the marine snail Nerita versicolor and characterized in depth. The most abundant of four, very similar isoforms, NvCla, was taken as reference and N-terminally sequenced to obtain a 372-nucleotide...

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